Antibiotics from gliding bacteria, LXXIX: Chemical modification of the antifungal macrolide soraphen A1α: Deoxygenation in the south-east ring segment

Article abstract of DOI:10.1002/jlac.199719970135

The present paper describes the chemical modification of the antifungal macrolide soraphen A_1α (1) by selective removal of oxygen substituents in the south-east ring segment. In the course of this investigation two key derivatives were prepared: 4-demethyl-5-O-(4-methoxybenzyl)-4-episoraphen (6) and 3,5-dideoxy-4-oxosoraphen (22). 6 served as precursor for 4-demethoxysoraphen (19) and 4-demethoxy-5-deoxysoraphen (20). 22 was used for the deoxygenation in positions C-3, C-4 and C-5 and for the synthesis of 3,5-didesoxysoraphen (24) as well as 4-demethoxy-3,5-dideoxysoraphen (27). The comparison of the antifungicidal activity of these derivatives showed that the OH group in position C-3 is essential for the biological activity of the soraphens. VCH Verlagsgescllschaft mbH, 1997.